Osborne makes history as first female jockey to win British Classic

Saffie Osborne made history on Monday at Doncaster when she rode Highwayman to a decisive win in the St Leger, becoming the first female jockey to claim a British Classic Flat race. The 24‑year‑old broke clear in the final stages of the 250th running of the world’s oldest Classic, turning the 11‑1 outsider into a champion and delivering a one‑two finish for trainer Joseph O’Brien, whose colt Enceladus was runner‑up. Pre‑race favourite Christmas Day, heavily backed to give Aidan O’Brien a fourth consecutive St Leger and complete a Derby‑St Leger double, faded to ninth, while Aidan’s other contender Amelia Earhart finished third. Osborne, who had not even known she would be riding the race until the morning, expressed surprise at the outcome, noting she “definitely didn’t have this on the bingo card this week.”

The victory carries significant weight beyond the personal milestone for Osborne, highlighting the slow but steady progress of women in top‑level flat racing. No female jockey has previously won any of the other four Classics—the 1,000 Guineas, 2,000 Guineas, Oaks and Derby—so her triumph shatters a long‑standing barrier. Osborne’s ascent has been marked by rapid achievement: she began her apprenticeship in 2020, finished second in the apprentice championship the following year, and dominated the Racing League as leading jockey for three straight seasons from 2022 to 2024. In 2024 she also became the first woman to win a race at the Dubai Carnival, and earlier that season she rode in her first Classic, finishing eighth in the 2,000 Guineas on Ten Bob Tony. Her background includes a lineage steeped in racing; she is the daughter of trainer and former National Hunt jockey Jamie Osborne and equine artist Katie O’Sullivan.

Joseph O’Brien’s continued success in the St Leger adds another layer to the story, as he now boasts victories both as a jockey—winning on Leading Light in 2013—and as a trainer, with wins in 2020 on Galileo Chrome and this year on Highwayman. Enceladus, who had shown top form with three major wins including the Gordon Stakes, was expected to be O’Brien’s best chance for a double, but Highwayman’s rapid improvement, highlighted by a Vinnie Roe Stakes win at Leopardstown, proved decisive. The result not only cements Osborne’s place alongside pioneers like Rachel Blackmore, the first female Grand National winner, but also signals a broader shift in the sport, suggesting that opportunities for female jockeys at the highest level may expand as trainers place greater confidence in their abilities.

⚡ Effects Interpreter